Let's Set Sail With Captain Morgan
by confetticas
Summary: Castiel is in love with his ridiculously straight best friend, but that's okay. Sam Winchester has all the answers, and also rum. Dean/Castiel and Sam/Gabriel. High school AU.


**Let's Set Sail With Captain Morgan (And Never Leave Dry Land)**

"And then," Castiel slurs, gesturing widely with the half empty bottle, "And _then_ he –"

Somewhere around the sixth 'and then' Sam gives up on Castiel ever making the point he's reaching for and suggests, "And then he murdered his little brother for getting you drunk in the basement of our high school?"

Castiel looks blatantly surprised, eyes scanning the room intently. "We're at school?" he asks, seeming honestly fascinated.

Yeah, Dean's going to kill him, Sam can accept this. In Sam's defense, Dean's the one who made Cas all high strung and bitchy so that Sam had no choice but to get him drunk to calm him down.

Oh, and that excuse is gonna stand up in court, too.

"Yes, Cas, we're at the school," Sam answers patiently. "In the basement. Where we've been for the last four hours. And you are never drinking my rum again."

Castiel's eyes widen and he gives Sam a pleading look, hugging the bottle to his chest. "But, Sam, that's… you wouldn't really do that to me, would you?"

"Holy fuck, have you been hanging out with Adam or something? That's just _wrong_," Sam complains loudly, looking anywhere but at Castiel's face and rather spectacular puppy dog eyes. "Fine, you're right, I wouldn't, but seriously man. Four hours. All you've done is whine and bitch about how my brother is an asshole, which is true, and that he's 'ridiculously straight', which is so far from true I'm still laughing inside."

Castiel crosses his arms and glares at the floor. "That isn't funny, Sam."

"Oh, god, it really is," Sam counters, shaking his head in exasperation. "First of all, Dean isn't straight and it doesn't take a genius to figure that out. Second of all, Dean is stupidly in love with you, and that also doesn't take a genius to figure out. Pull yourself together and at least _try_ before you resign yourself to, what was it you said? A 'miserable, unfulfilling, lonely life without the most amazing man you've ever known?'"

Castiel flushes slightly. "Sam," he protests in annoyance.

Sam smirks slightly. "C'mon, Cas, it's not so tragic as you're making it out to be. Give it a shot, at least. You can't give up before you've tried, it's pathetic, and you aren't pathetic."

Castiel bites his lip, visibly torn. "What if you're wrong and I ruin everything?" he asks, blue eyes wide and forlorn. "Dean is my best friend. I don't want to lose him."

"Oh, _come on_," Sam scoffs, grabbing Castiel's hand and pulling him to his feet. "I tried being nice, but really, this is just getting ridiculous. Man the fuck up and go tell my brother that his unrequited crush isn't so unrequited after all."

Castiel pulls his arm out of Sam's grasp and sits back down on the floor, glowering. "Why don't _you_ man the fuck up and go tell _my_ brother that you're stupidly in love with him?" he counters, which is sort of a valid argument.

Sam flounders for a response for a minute before he nods once and pulls Castiel up onto his feet yet again. "C'mon," he says brightly, pulling Castiel towards the stairwell, pausing every few steps to let the considerably more intoxicated boy regain his balance. "This is sad and pathetic," he adds cheerfully as he drags Castiel through the empty, darkened hallways of their high school. "Is this the first time you've ever even looked at alcohol or something?"

Castiel flushes and doesn't answer, which is as good as answering.

"Oh my _god_," Sam exclaims as he stops in his tracks and studies Castiel, who in turn studies the floor. "You can't be serious," he protests.

"I… have self control, unlike some of us," Castiel mutters defensively.

Sam snorts derisively. "Riiiiight, half a bottle of Captain's later, you just keep singing that song, Cas," he mocks, thoroughly annoyed. "Where's Gabriel?" it occurs to him to ask.

Castiel looks bewildered. "What does Gabriel have to do with anything?"

"You told me to go tell your brother that I'm stupidly in love with him," Sam reminds him, drawling the words out nice and slow. "So, I'm going to go tell your brother that I'm stupidly in love with him. It would help if I knew where to find him."

"…I didn't think you'd actually _do_ it," Castiel says, staring at Sam with wide eyes. "You're going to go tell Gabriel that you love him."

Sam rolls his eyes. "I'm going to go tell Gabriel that I have vaguely affectionate feelings for him and would like to see where they take us," he corrects smoothly.

"Right now," Castiel clarifies. "You're going to tell him this right now, for no better reason than to prove that if you can do it, so can I?"

"Well, I wouldn't be doing it if it weren't true," Sam points out rationally. "I'm not inclined to sit around and mope about something when I don't even know that it's true. I like Gabriel, I'm pretty sure he likes me, so I'm going to go tell him that I like him and see where it goes. You like Dean, Dean likes you, and you're both too stupid to do anything about it. I can see which one of these situation is going to end in more enjoyment, can't you?"

Castiel narrows his eyes suspiciously. "I'll believe that you're going to do this when I see you do it," he says stubbornly. "And not a second before. Gabriel should be at Michael's apartment."

Sam nods, determined and cheerful and just drunk enough to miss the possible idiocy involved in his plan. "Let's go, buddy," he chirps, slinging an arm over Castiel's shoulder and dragging him along.

Castiel follows easily, mostly because he's too busy staring at Sam like he can't fathom the sheer stupidity Sam's exhibiting. "Seriously?"

"Yup," Sam agrees, sounding almost excited now. "Now hush. I'm plotting."

Castiel grumbles something decidedly impolite under his breath, but doesn't otherwise protest. Besides, he figures, if Sam's plan ends in disaster, it will undoubtedly be hilarious, and prompt Sam to share more rum. If his plan is successful, maybe Castiel will work up the nerve to say something to Dean. It's pretty much win-win, in Castiel's opinion.


End file.
